Strategic Horizon
Rolling view: 3 months back → now → 6 months forward Last updated: March 3, 2026
Strategic Arcs
Multi-month initiatives tracked as narrative threads. Each arc represents a question the portfolio is trying to answer over 6-18 months.
1. Scaling Without Me
Phase: Early proof → Building pipeline | Horizon: 18 months
Can workshops run without Reuben in the room — and still be good? This is the existential question for the capacity building model. The answer so far is yes, with caveats.
Where it stands now: Two independent facilitators are running sessions (Courtney Garza at TCEA, Anna-Lena in Paris). Gregory Wilson is beginning Build-a-Bot facilitator training (first walkthrough Mar 3). ISTE partnership scoping is complete — train-the-trainer for 3 ISTE faculty is the next concrete step. CRM re-engagement (5 drafted emails to stale facilitators) is blocked on model clarity.
The key question right now: What does quality look like when someone else runs it? The ISTE partnership will be the first real test of a formalized train-the-trainer pathway. Gregory’s training is the first Build-a-Bot-specific version.
Next milestone: Gregory completes facilitator training and runs a session (target: Tinkery Flash Lab, Mar 30). ISTE TTT terms formalized.
2. Research Validation
Phase: Experiments running | Horizon: 12 months
Can Build-a-Bot and Flash Lab be validated through research — not just testimonials? The portfolio has strong anecdotal evidence (“I made a thing!”) but thin research evidence.
Where it stands now: Three research-adjacent threads are active. LabGPT is Cathy’s pilot study testing two conditions (Critic vs. Co-designer) — a real RCT using Build-a-Bot platform architecture. Health Coach Bot (Marily Oppezzo / Michele Patel) is reactivating — if they get a grant, it validates Build-a-Bot as a research tool, not just a workshop activity. Colombia chatbot (Ana Saavedra) ran its school study and is in data export/wrap-up.
The key question right now: Will any of these produce a publishable result or a funded grant application that names Build-a-Bot as infrastructure? Marily’s connection to dean Dan Schwartz makes Health Coach Bot politically visible even beyond its research value.
Next milestone: Health Coach Bot meeting (Mar 3) — clarify research direction. LabGPT study runs (Mar 4, Mar 9) — condition guardrails tested. Colombia data exported and thread closed.
3. Revenue Model
Phase: First pricing experiment | Horizon: 12 months
What’s the sustainable funding model? Josh’s three pillars (Playbook, Reach, Revenue) demand a pricing answer. The Feb 25 ISTE meeting was the first time pricing was discussed in a real partnership conversation.
Where it stands now: Market research is done — $5K baseline for a facilitated session, $15K-$25K for a TTT cohort. ISTE is the test case for an “authorized provider” model. But no money has changed hands yet. The question of whether this flows through OTL, through a Stanford entity, or through ISTE directly is unresolved.
The key question right now: Will ISTE agree to terms that include revenue? And what’s the institutional mechanism — OTL licensing, direct contract, or something else? Isabelle is pursuing the OTL + dean conversation.
Next milestone: ISTE partnership terms formalized (target: March). First revenue data point from any partnership engagement (target: June).
4. International Reach
Phase: Signals confirmed, pipeline unbuilt | Horizon: 18 months
Is demand beyond the US real — and can it be served without burning out? Oman, Paris, Colombia, and Australia all represent genuine interest, but each was opportunistic rather than systematic.
Where it stands now: Oman delivered (Feb 2-5) with strong feedback and a whitepaper follow-up thread. Anna-Lena runs independently in Paris (peak [MULTIPLIER]). Colombia study completed. Australia (Kelly/Churchill) is still back-burner. LAUSD Foundation meeting (Mar 19) is domestic but represents district-level scale.
The key question right now: Is the international play “we train people who then serve their own regions” (the Anna-Lena model) or “we deliver internationally” (the Oman model)? The first scales; the second doesn’t.
Next milestone: CRM re-engagement includes Spyros at RMIT (2,000 students, March/April window closing). Self-service toolkit maturity (designkit.stanford.edu + bot101.app) determines whether the Anna-Lena model can replicate without direct training.
5. Seed Grant Ecosystem
Phase: Framework built, execution starting | Horizon: Ongoing
Can the seed grant lifecycle (SPARK → BUILD → SHARPEN → SCALE) become a real curriculum spine — not just a diagram? The Three C’s framework (Critical Boost, Capacity Building, Cross-Pollination) mapped beautifully onto the four phases, but most of the proposed offerings haven’t been built yet.
Where it stands now: SCALE phase is well-covered (4 workshops in 12 months: Scaling Sustainably, Partnerships as Pathways, Legal 101, Comms Workshop planned Mar). The middle phases (BUILD/SHARPEN) have two proposals each but none delivered. Cross-cohort offerings (Legal 101) proved the model — pulling seed grantees, tEquity, and Create+AI into one room worked.
The key question right now: Which 1-2 new offerings from the lifecycle framework should be prioritized for Q2? And who co-facilitates them? The seed grants themselves are going quiet (DeVeaux stalled, King ambiguous, Fan/Forssell low-touch), which threatens Goal 1’s tag coverage target.
Next milestone: Comms Workshop delivered (Joe lead, Mar 2026). Decision on Q2 offerings at a Josh 1:1. DeVeaux formally marked inactive.
Monthly Themes
December 2025 — “Building the Foundation”
The month before liftoff. CRM views were built, dashboard infrastructure expanded, Build-a-Bot start messages refined, and the Colombia chatbot took shape for Ana’s school testing. Oman prep consumed the second half. Beneath the surface: the shift from “I do workshops” to “I build systems that enable workshops” was becoming visible — designkit.stanford.edu launched, bot101.app crossed 1,000 bots, and the facilitator pipeline concept started forming.
Key decisions: Committed to Oman trip. Paused Health Coach Bot and VFT iOS to make room.
January 2026 — “Setting the Table”
GPS goals finalized with Josh. Capacity analysis surfaced 18 active threads and recommended trimming to 14. Jury duty week (Jan 26-31) created unexpected thinking time. CRM re-engagement campaign planned (5 priority contacts drafted). Vanessa Monterosa call opened the NewSchools thread. Anna-Lena debriefed her Paris Flash Labs — researchers preferred “Research Design” framing over “Build.”
The real theme: articulating what the work is. Josh kept asking “What’s your model?” — the question that would drive February’s strategic push.
Key decisions: Crystal Springs removed. VFT iOS paused. Health Coach Bot paused. Five CRM re-engagement emails drafted.
February 2026 — “The Model Takes Shape”
The breakthrough month. Oman Hackathon delivered (week 1). AI+Education Summit attended (week 2). Legal 101 ran as the first cross-cohort offering (week 3). ISTE partnership meeting hit a major milestone with Joseph South and Isabelle (week 4).
Strategically: the Three C’s framework mapped to a seed grant lifecycle (SPARK → BUILD → SHARPEN → SCALE). The capacity building model doc answered Josh’s “What’s your model?” question with three pillars: Playbook, Reach, Revenue. Market research on 9 comparable orgs grounded the pricing conversation. The Personal Logic Model emerged as a reflective practice artifact. Courtney Garza completed Build-a-Bot training, then took the initiative to register and deliver it at TCEA on her own — strongest scaling proof point yet.
Key decisions: ISTE pivoted from 60-min session to train-the-trainer. $5K baseline pricing proposed. Three personas framework (Instructional Practices, Contextual Curiosity, Identity) crystallized post-workshop pathways.
March 2026 — “Testing the Model” (current)
The model built in February meets reality. Gregory Wilson begins Build-a-Bot facilitator training (first formal walkthrough). Health Coach Bot reactivates with strategic framing (research validation + dean connection). LabGPT condition guardrails get built for Cathy’s study. ISTE follow-ups and due diligence continue. LAUSD Foundation meeting (Mar 19) could open district-level Flash Lab demand.
March is dense: 20 active threads (up from 18 despite 4 completions), a Stanford trip at month-end (Tinkery Mar 30, Lake Forest Mar 31 - Apr 1), and key decisions pending on CRM timing, King/Our Voice ownership, and Health Coach Bot scope.
Key questions this month: Does Gregory’s facilitator training work? What does Marily’s research direction look like? Can ISTE terms be formalized? Is LAUSD real?
April 2026 — “Facilitators in the Field” (forward look)
If March goes well, April is when facilitators start running sessions. ISTE TTT Week 1 (Reuben runs train-the-trainer). Tinkery toolkit v1 lands (Gregory collaboration). Lake Forest / PLEX visit happens (Christine partnership). DeepLearning.AI Dev Day (Apr 28-29) provides industry perspective.
Watch for: Quality signals from Gregory’s first independent session. Whether ISTE facilitators are ready to co-facilitate by month-end. Health Coach Bot scope decision ripple effects.
May 2026 — “First Independent Sessions” (forward look)
ISTE facilitators co-facilitate their first Flash Lab with Reuben observing. NewSchools engagement (if Vanessa timeline holds). LabGPT/CRAFT protein synthesis RCT (May 5). This is the month where “Scaling Without Me” either works or exposes gaps.
Watch for: Quality of ISTE-facilitated sessions vs. direct delivery. Whether the self-serve toolkit is sufficient for new facilitators. Research results from LabGPT study.
June 2026 — “Revenue Signal” (forward look)
ISTE facilitators run their first fully independent session + debrief. First revenue data point from a partnership engagement. Mid-year capacity check: is the portfolio sustainable at current pace?
Watch for: The first dollar. Whether “independent” actually means independent or whether Reuben is still getting pulled in for support. End-of-Q3 goal assessment prep.
July 2026 — “Mid-Year Scorecard” (forward look)
Playbook/Reach/Revenue scorecard for Josh. Mid-year GPS review. Decision point: what arcs are working and what gets pruned? The 5 Questions exercise (from capacity building model doc) gets its first real-world answers.
Watch for: Facilitator retention — are trained facilitators running repeat sessions or was it one-and-done? International pipeline health.
August 2026 — “Scale or Stall” (forward look)
ISTE fall convening prep (90-educator kickoff, 1.5 day in-person). NewSchools Venture Fund engagement (if timeline holds). Annual goal deadline approaching. This is the month that determines whether the scaling model is real or aspirational.
Watch for: 8-10 trained facilitators target. 15-20 sessions by others target. Whether the “Scaling Without Me” arc has moved from proof-of-concept to operating model.
Arc × Month Matrix
| Arc | Dec ‘25 | Jan ‘26 | Feb ‘26 | Mar ‘26 | Apr ‘26 | May ‘26 | Jun ‘26 | Jul ‘26 | Aug ‘26 |
|---|---|---|---|---|---|---|---|---|---|
| Scaling Without Me | Toolkit live | CRM drafted | Courtney TCEA, ISTE scoping | Gregory training, ISTE terms | ISTE TTT, Tinkery v1 | ISTE co-facilitation | First independent | Scorecard | Fall convening |
| Research Validation | Colombia building | Colombia testing | LabGPT conditions, ABCs use | Health Coach Bot, LabGPT study | CRAFT RCT prep | LabGPT RCT (May 5) | Results analysis | Publications? | — |
| Revenue Model | — | — | Market research, $5K baseline | ISTE terms | OTL process | — | First revenue? | Revenue review | Pricing v2 |
| International Reach | Paris ongoing | Anna-Lena debrief | Oman delivered, whitepaper | CRM re-engage? | RMIT window | — | — | Pipeline check | Australia? |
| Seed Grant Ecosystem | Low-touch | Capacity analysis | Lifecycle framework, Legal 101 | Comms workshop | Q2 offerings? | Mid-point check-in | — | New cohort? | Curriculum review |
Update cadence: Monthly (during end-of-month prep). Quick scan during weekly review. This is a personal strategic reflection artifact — narrative lens, not task list.
reference/strategic-horizon.md